Born in Yonkers, New York, Michelle Morales was a self-described “military brat,” spending her childhood moving around the country before settling in Chicago in 1993 to attend DePaul University. For most of her professional career, Morales worked in the field of alternative education with a focus on advocating for educational justice.
In 2015, Morales became the executive director of the Illinois chapter of the Mikva Challenge, an organization that creates space for youth civic participation and leadership. But by 2019, the demands of unrelenting, high-stakes fundraising began to take its toll. “I internalized the pressure that fundraising not only provided programs for young people, but that the livelihood of my staff depended on my fundraising prowess, and that started to get to me,” she told me on a recent call. Morales started looking for work in philanthropy, and in April of 2019, she noticed that Woods Fund Chicago was looking for a president.
The foundation traces its origins to the Woods Charitable Fund, which was founded 80 years ago by philanthropists Nelle and Frank Woods. In 1993, Woods Fund Chicago was incorporated as a private, independent foundation, and 11 years later, former grantee, advisory committee member and board member Barack Obama was elected the first board chair without a connection to the Woods family. In 2008, Woods Fund became one of the first foundations in Chicago to center racial equity in its grantmaking. The foundation had $52 million in total assets and disbursed $3.8 million in grants in 2021.
Morales said she “stared at the posting for about three weeks” before applying. She landed the job and officially assumed the role in November 2019. During her tenure, Woods Fund Chicago has gone all-in on trust-based philanthropy, rolled out the Movement Building for Racial Justice Fund, and announced it would dramatically increase its grantmaking payout to 11%, starting in 2023.
I chatted with Morales as she and her team were in the process of standing up a pooled fund to serve Chicago’s migrant asylum seekers. Here are some excerpts from that discussion, which have been edited for clarity and length.
Who are your biggest influences?
This may sound cliché, but my family is definitely a huge influence. My parents were migrants from Puerto Rico, and watching them struggle definitely influenced my trajectory toward social justice. I am also very lucky to have been a community organizer in the larger Puerto Rican independence movement. I know several folks who were engaged in the struggle for independence and are still involved in Chicago’s Puerto Rican community, and that has really influenced me, especially as you get older and want to stay politically active.
Can you think about a time when things didn’t work out for you as planned, but looking back, it turned out to be a blessing?
This may sound crazy, but I’m going to say the pandemic. I started at Woods Fund in November 2019 and had plans to dig deep into the foundation, and then the pandemic hit. All of the plans were scrapped because of the urgency of the moment, which then was followed by the uprisings after the murder of George Floyd.
We made changes within the foundation, and I don’t think we would have made them so quickly without the pandemic. Instead of cutting checks for grants, we moved to automated clearinghouse payments. We quickly moved from paper grant agreements to using Docusign. Then there were the bigger initiatives around embedding trust-based philanthropy, like doing away with reports and applications.
From a personal perspective, the pandemic forced us all to slow down, and as someone who is a self-described workaholic, that was also a blessing, because it allowed me to spend more time at home and with my family.
To that point, how do you try to separate your professional life from personal?
It’s difficult, especially when you’re a foundation leader. I’m representing Woods Fund all the time, and that’s something I take very seriously. I’m always careful about how I engage and what I say on social media. And I’m so involved with the community that a lot of times, I’m engaging with organizers and taking that work home with me.
I did implement one little thing to separate my professional and personal life. I started it early in the pandemic when we were fully remote, and it’s that I still get “dressed for work” when I’m working from home. It might not be super fancy, but I still get dressed, and then at the end of the workday, and I get changed into something more comfortable.
You probably know this, but research has shown that remote workers are more effective when they ditch the sweat pants and dress up a little bit.
Oh, I totally agree with that. Even if it wasn’t for that fact my brain needs to know, “Oh, you’re done working now because you have changed into your pajamas.” [laughs] It’s also a signal to my family. I remember, especially when we were remote five days a week, my husband and son would say, “Oh, you’re done working now?” because they’d see that I changed my clothes.
You’ve used your platform to raise awareness and consciousness about the power of youth voice. Can you talk more about why that issue is so important to you?
I’m 47 now, I’m turning 48 this summer, so I started working in alternative education when I was 21, after I graduated from DePaul. Very early on, I noticed that young people weren’t taken seriously, as if young people do not have enough wisdom to really impart any insight.
We blame young people for not being involved and yet, at the same time, we’re dismissive of them. We can’t have it both ways. If we say that young people are our future, you have to start engaging them and take what they have to say seriously. So when I started the Mikva Challenge in 2015, we pushed back on that notion. We elevated youth voice through youth councils who would meet with legislators and elected officials.
I believe that young people, even down to kindergarten, should have the right to have their insights respected. Because with the way things are now, you may not be taken seriously when you’re 18. That’s a long time to go without your voice being respected.
We see funders focus on engaging college students, which is very important, but as you suggest, the window of engagement may have closed for some of these people because they’ve been ignored for the past 10 years.
Oh, absolutely. We had data at the Mikva Challenge that showed that if you engaged young people as young as 12, they stayed engaged throughout their entire lives. One of the challenge alums is my alderman. They’re engaged in campaigns, they’re lawyers writing legislation. It shows that if you activate young people as young as possible, it stays with them throughout their lives.
What’s the one book you’d encourage our readers to check out?
As someone who leads a foundation, I’m obsessed with anything management related. Your readers may know this book, but I cannot encourage it enough — it’s “The Four Pivots: Reimagining Justice, Reimagining Ourselves,” by Dr. Shawn A. Ginwright, and it’s an amazing book that asks people to think differently about leadership.
For those of us who are working in racial justice, this becomes especially important because we need to lead in a way that I don’t think exists yet, because many of the traditional leadership norms and management styles run counter to racial justice. So this book came to me at a very transformative time, as I was dealing with a pretty significant health crisis while also thinking about what it meant to lead in a foundation that was committed to racial justice.
Can you provide an update on Woods Funds’ pooled fund for Chicago’s migrant community?
We’re standing up a pooled fund to address the current migrant asylum seeker crisis in Chicago and begin the process of creating shelter infrastructure that would support future migrants and the unhoused population.
It’s going to hopefully provide mutual aid funding for groups that are on the ground providing emergency resources to migrant families. We are also going to look at increased grantmaking for the 501(c)(3)s that we support that are on the verge of burning out because they’ve hit their staffing capacity. And we’ll support capital improvements to shelters and respite centers, as well as churches and other buildings that could serve as future housing opportunities.
We’re in the planning phase right now, and we’ll be doing a full funders briefing June 12 to engage the funding community. We hope to have the funds stood up by the end of June, so we’re moving very quickly.
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